Day 1 | Arrive in Chicago, IL

Distance: 0.00 miles / 0.0 km

Arrive at the airport and proceed to your hotel. Chicago is a city with a rich history and a musical soul. From the towering skyline to the smoky lounges where you can hear jazz and blues, Chicago offers a special treat for anyone with a special interest. Consider a visit to the Art Institute of Chicago. This museum is home to one of the best and most diverse art collections in the world including the world''s largest group of Monet paintings. The most prominent structure in Chicago is the Sears Tower. While no longer the tallest building in the world, the Sears Tower stands proud at 1,454 feet high. A seventy second elevator ride will propel you to the skydeck on the 103rd floor for a bird''s eye view of Lake Michigan, both the North and South Sides of the city, the surrounding suburbs and, on a clear day, parts of Indiana, Wisconsin and Michigan. Informational exhibits illustrate the history of Chicago and the construction of the tower. Visit Millenium Park for a look at the famous Kapoor Sculpture. Inspired by liquid mercury, the sculpture has striking reflections of the Chicago skyline and is among the largest of its kind in the world.

Accommodations: Quality Inn Schaumburg or similar (2 night)

Day 2 | Chicago, IL

Distance: 0.00 miles / 0.0 km

Today is yours to explore other Chicago attractions. Take a guided tour of the Frank Lloyd Wright Home and Studio. Architect Frank Lloyd Wright began building this house in 1889 and continued to make unique additions until it suited his personal needs. For a bite to eat with a spectacular view of the city, visit the John Hancock Center. After 40 seconds in the John Hancock''s elevator, you are transported many stories above Chicago. From there, the city''s third-largest building offers views that stretch out to 80 miles on a clear day. For a fun afternoon, fair style, visit Navy Pier. Since 1916, Navy Pier has been home not only to the military but to scores of special attractions. The pier offers everything from an IMAX theater to performances by a Shakespeare troupe. View dancing in a grand ballroom, ride the splendor of a fifteen-story Ferris wheel (a replica of the one at Chicago''s 1893 World''s Fair), or relax to the sounds of waves quietly lapping on the lakeshore. For a cultural encounter, visit one of the unique neighborhoods in Chicago like Chinatown or Little Italy. Both offer cultural food specialties and family-owned restaurants and shops. This evening venture out to one of the many lounges offering live musical entertainment featuring jazz and blues.

Day 3 | Chicago – Bloomington – Springfield, IL

Distance: 205.00 miles / 329.8 km

Pick-up your rental car,leave Chicago and drive toward Springfield for an overnight stay. Along the way you will encounter the town of Bloomington home of the Historic Route 66 Memory Lane. Along Historic Route 66 this traditional park features restored billboards, classic business banners and Burma-Shave signs on a quaint tree-lined scenic road into downtown Lexington. Continue to Springfield for an overnight stay. Springfield became the Illinois state capital in 1837 with the help of a young lawyer and politician named Abraham Lincoln. He lived in the city until he left to become the 16th President of the United States, in 1861. From that moment on, the city’s history and future have been inevitably tied to this most famous and beloved American citizen. Visit The Lincoln Home National Historic Site, the Lincoln Depot, and the Lincoln Tomb which, among many others, are the most popular attractions of this area. You can also ride to all the Lincoln historic sites, museums, the Dana-Thomas House and the State Capitol building aboard the Elijah Iles trolley. Accommodations: Best Western Springfield or similar (1 night)

Day 4 | Springfield – St. Louis, MO

Distance: 102.00 miles / 164.1 km

Today, drive toward Missouri. Saint Louis is the largest city on Route 66 between Chicago and Los Angeles. It was founded on the banks of the Mississippi River in 1762 and became the "Gateway to the West". Lewis and Clark left St. Louis on their famous journey across an unfamiliar land to the Pacific Ocean. Route 66 came through here in 1926 and continued the traditions of travel. The famous St. Louis Gateway Arch serves as a symbol for the conquest of the West. In the early 1900''s, St. Louis gained international acclaim for hosting the World''s Fair, the Olympics, and the first International Balloon Race. Visit Union Station a wonderful example of historic preservation and once the busiest railway station in the world. Its unique architecture is modeled after the walled medieval city of Carcassone in southern France. It was restored and converted into a shopping center. By the same token, Saint Louis boasts many historic homes, such as the Daniel Boone Home and the Campbell House Museum. Or, take the time to visit Grant’s Farm. This farm once belonged to Ulysses S. Grant, America’s 18th President, and was then purchased by the Busch family almost a hundred years ago. Today, the estate compliments of Anheuser-Busch, is a wildlife preserve. Travel in an open-air coach past Mirror Lake to Grant''s Cabin, constructed by him in 1856. Ride past Deer Park and view bison, elk, antelope, zebras, llamas and ostriches. See the famous Clydesdales in their pastures next to the stables. Around Saint Louis you will find pieces of the past including diners and petrol stations. One place to stop is Ted Drewes; they have been selling frozen custard in St. Louis since 1930.

Accommodations: Best Western Saint Louis Inn or similar (1 night)

Day 5 | St. Louis – Rolla – Springfield, MO

Distance: 218.00 miles / 350.8 km

Depart St. Louis and continue on the trail of this historic road. Your next stop will be Rolla, home of the Totem Pole Trading Post, built in 1933. Note the curbs on the roadside, these where intended to make sure traffic stayed on the road, only to tip cars over in practice. Continue on to Springfield which is recognized as the birthplace of Route 66 since on April 30, 1926, officials in Springfield proposed the name for the new Chicago-to-Los Angeles Highway. Traces of the Mother Road are still visible along the streets of Springfield. The red booths and gleaming chrome in diners, the stone cottages of tourist courts and the now-silent service stations that saw America fall in love with the automobile. Springfield mixes its past with the future as historic Route 66 borders downtown Jordan Valley Park, the colorful downtown area, the city''s square and the site of several historic events as it bypasses the city on the north side. Take a moment and enjoy the interesting shops and creative eateries that surround the historic downtown area. Here you will enjoy a variety of delicious cuisines, flea markets, novelty stores, boutiques and night clubs. Accommodations: Clarion Hotel Springfield or similar (1 night)

Day 6 | Springfield – Joplin – Tulsa, OK

Distance: 181.00 miles / 291.2 km

Leave Missouri behind today and drive toward historic Oklahoma. On the way there, visit Dale''s Old Route 66 Barber Shop on the corner of Utica St. and Euclid Ave in Joplin for a real bit of nostalgia. Continue on your journey to Tulsa. By the 1920''s, Tulsa was a boomtown and dubbed by many as the "Oil Capital of the World." Business is still booming with a thriving aerospace industry and a number of major corporations situated here. Architecture fans shouldn’t miss the Art Deco façades at the Boston Building, Union Depot, and the Philtower. The Philbrook and the Gilcrease museums are the place for art lovers. The Gilcrease contains a copy of the Declaration of Independence. For something different, enjoy the beautiful grounds of Oral Roberts University. Oklahoma is rich with Native American influence, culture and history. Visit the Cherokee Heritage Center at Tsa-La-Gi. At the Cherokee Heritage Center, you can experience Cherokee life the way it was before it was touched by European influences. You will witness tasks such as food preparation, basket weaving, weapon making and recreation. Have a first-hand view of Cherokee crafts such as pottery and jewelry. While at the center, be sure to visit the museum and ancient village, as well as the Ho-Chee-Nee Prayer Chapel and Cherokee Hall of Fame. Beloved cowboy Will Rogers was born and raised in Tulsa. Visit his birthplace and memorial to learn more about his life.

Accommodations: Holiday Inn Select Tulsa or similar (1 night)

Day 7 | Tulsa – Oklahoma City, OK

Distance: 108.00 miles / 173.8 km

Depart Tulsa this morning and drive toward the Oklahoma’s state capital, Oklahoma City. It is at heart a cowboy town and this can be seen at Stockyards City. It was founded in 1910 and is popular for its restaurants and shops specializing in Western wear, custom-made boots, and saddles. It is located next to the Oklahoma National Stockyards, which claims to be the largest live cattle market in the world. Cattle auctions, open to the public, are held all day Monday and Tuesday. Visit the National Cowboy Hall of Fame & Western Heritage Center .The history and culture of frontier life are depicted in a wide range of exhibits in this large-scale museum. Paintings by well-known artists Charles Russell and Frederic Remington are the highlight of the Atherton Art Gallery. The American Rodeo Gallery features a bunkhouse, a display of brands and a barbed wire collection. Walk through Property Junction, a life-size recreation of an authentic frontier town. Visit the revitalized Bricktown Canal, constructed by excavating an old street. Many restaurants and clubs built patios to take advantage of the view. Water taxis are a popular and enjoyable means of transport between shops, cafes, and nightclubs here. The Paseo Historic District has galleries, studios, and restaurants in a historic part of town. This artists'' community, which resembles a Spanish Village with stucco buildings and clay tile roofs, serves as home to writers, painters, potters, photographers, dancers, and actors. Enjoy studio visits, performances, shopping, and dining in this delightful area.

Accommodations: Quality Inn Southwest or similar (1 night)

Day 8 | Oklahoma City – Shamrock – Amarillo, TX

Distance: 260.00 miles / 418.3 km

Leave Oklahoma City behind and drive toward the Lone Star State today. As you head into Amarillo make a stop in the town of Shamrock to visit the U-Drop-In Restaurant and Service Station dating from 1936 and the Pioneer West Museum, located in the historic Reynolds Hotel, for a glimpse on how life was in these parts when Route 66 was indeed the Mother Road. Continue to Amarillo. The combination of the railroad and ranchland has made Amarillo a cattle-shipping capital. While agriculture remains the foundation of the economy, Amarillo''s location on a famous major highway, Route 66, has given way to making it a tourist destination. A must see is the Cadillac Ranch; this roadside attraction features 10 graffiti-covered Cadillacs standing upright in a row, buried nose-first in the ground. The sculpture is the brainchild of Amarillo millionaire Stanley Marsh III, who chose classics dating from 1948 to 1963, the "Golden Age" of the American automobile. Visit Route 66’s Historic District. This mile-long stretch of road originally belonging to Route 66, now features shops, clubs and restaurants. The American Quarter Horse Heritage Center & Museum showcases the development of the American Quarter Horse from colonial times to present day is traced through interactive exhibits, dramatic video presentations and live demonstrations. Several locals host horse-drawn wagon rides through miles of scenic ranch land followed by mouth-watering meals.

Accommodations: Best Western Amarillo Inn or similar (1 night)

Day 9 | Amarillo – Tucumcari – Santa Rosa – Albuquerque, NM

Distance: 289.00 miles / 465.0 km

Leave Big Texas behind as you drive into the southwestern charm of New Mexico. First on this road you will encounter the town of Tucumcari. Here you will find the beautifully restored Blue Swallow Motel with its famous blue neon and the Tucumcari Historical Museum where you can experience the legendary past of this town. Next on the way is the town of Santa Rosa which contains more that ten structures still in operation from the glory days of Route 66. Continue to Albuquerque for a two-night stay. Albuquerque is New Mexico''s largest city and a study in contrasts: old and new, natural beauty and manmade wonders, frontier town and sophisticated metropolis. Even the landscape, which accommodates both majestic mountains and vast desert plains, reveals the area''s diversity. Albuquerque is also blessed with a wide cultural mix that is reflected in all aspects of day-to-day life. Places worth visiting are the historic Old Town, trendy Nob Hill and the Indian Pueblo Cultural Center. Take a ride on the Sandia Peak Tramway. This 20-minute excursion is the world''s longest aerial tram ride, and also one of the most scenic. Once at the top, you may like to ski, mountain bike, or just enjoy the view. There are restaurants at both the top and the bottom

Accommodations: Quality Inn and Suites Albuquerque or similar (2 nights)

Day 10 | Albuquerque – Santa Fe – Albuquerque, NM

Distance: 0.00 miles / 0.0 km

Today take a short drive to neighboring Santa Fe, the oldest capital city in the United States. Flanked by crooked streets and Pueblo style buildings, Santa Fe has an old world feel with a central plaza where you will find many shops, restaurants and art galleries. Santa Fe is known as the “City Different” because of the blending of cultures which is reflected in the harmonious inhabitants and different architectural styles. Visit the Mission San Miguel. The San Miguel Mission, the oldest church in Santa Fe, was built in 1626 for the servants brought to Santa Fe by the Spanish. The mission was damaged during the Pueblo Revolt in 1680 and was rebuilt in 1710. View the famous “Miraculous Stairway” at the Loretto Chapel. Legend holds that a carpenter mysteriously appeared to build a staircase to the choir-loft. Amazingly, he used no nails or supports to build the corkscrew staircase and then disappeared before he could be paid. A remarkable view can be had from The Cross of the Martyrs, located on a small hill on the 600 block of Paseo de Peralta. It serves as a reminder of the 21 Franciscan monks that were slain during the Pueblo Revolt. For a peek into history, visit the "Oldest House." It dates back to approximately 1766. Inside the house are the remains of a Spanish warrior. You can also view a display of traditional weavings.

Day 11 | Albuquerque – Gallup – Holbrook, AZ

Distance: 233.00 miles / 374.9 km

Depart Albuquerque via Gallup. This small town’s two known Route 66 landmarks were lost to fire in past years; all that remains is the actual road. Press on into Arizona. Holbrook, Arizona became a frontier town in 1881 and it has remained so ever since, only the theme has changed. Historic Route 66 provided a means for those seeking better futures after World War II. Close by are the ancient Native American lands of the Navajo and Hopi Indian Nations. Also nearby is the Petrified Forest National Park. There is an abundance of beautifully colored petrified logs that existed 225 million years ago. The 28-mile drive through the park has scenic overlooks, wonderful photo opportunities are found at Rainbow Forest, Agate House and Blue Mesa. Part of the Painted Desert also lies within the park where many hardened dunes can be found. These hardened dunes are spectacular bands of grays, reds, oranges and yellows. The area is especially beautiful at sunset and sunrise when the land appears to glow in hues of violet, blue, red and gold. This evening, explore Holbrook’s Main Street for shopping and dining.

Accommodations: Best Western Adobe Inn Holbrook or similar (1 night)

Day 12 | Holbrook – Winslow – Grand Canyon National Park – Flagstaff, AZ

Distance: 177.00 miles / 284.8 km

This morning depart for Grand Canyon National Park which is located close to this route on the way to Flagstaff. On the way, the town of Winslow offers The Old Trails Museum and the Minnetonka Trading Post whose façade is made of petrified wood. Continue to the Grand Canyon. The overwhelming size and brilliant colors of the Grand Canyon easily make it one of the natural wonders of the world. The Grand Canyon was carved out by natural elements including the Colorado River over vast geological spans of time. The South Rim has an assortment of viewing areas that can be reached by shuttle or car. There are many paved and unpaved walkways along the rim. Visit the Bright Angel Lodge for an excellent vantage point. The lodge is a historic landmark and also offers a gallery, restaurant, exhibits and a great view. Guided hikes also leave from the lodge and talks are often offered by the park rangers. For the adventurous, hiking trails and guided mule rides will take you down to the Colorado River. Rafting trips along the river are also a spectacular way to enjoy the canyon.

Accommodations: Best Western Pony Soldier or similar (1 night)

Day 13 | Flagstaff – Las Vegas, NV

Distance: 277.00 miles / 445.7 km

Leave the natural wonder of the Grand Canyon behind as you drive toward Las Vegas this morning. Even though, Las Vegas and, as a whole, the state of Nevada do not form part of this historic route, it is such an impressive highlight that is worth the deviation. Las Vegas has something to offer everyone. From the outrageous live shows to the excitement of casinos, the action never stops from morning to night. Stroll down Las Vegas Boulevard, also known as “the strip.” Each hotel and casino has a distinctly different theme and all are wondrous displays. Take a trip up to the top of the Stratosphere hotel tower, the tallest building west of the Mississippi River. Enjoy dinner at the Top of the World, or simply admire the view from the observation deck. Visit any of the premier hotels including Caesars Palace, The Venetian and Paris for luxury shopping. If you’re searching for a bargain, drive to one of the outlet malls featuring designer names at discounted prices. Make sure not to miss the nightly fountain show at the Bellagio Hotel. Using a dramatic combination of music, water and light, the Bellagio delivers spectacular performances nightly with its majestic fountains. For a different side of Vegas, visit Fremont Street. This historic street features shops, restaurants and casinos. Above you hangs a canopy screen where more than 12 million lights put on a spectacular show. Enjoy an overnight stay in Las Vegas.

Accommodations: Best Western Mardi Gras Inn and Casino or similar (1 night)

Day 14 | Las Vegas – Barstow – Santa Monica, CA

Distance: 287.00 miles / 461.8 km

Leave the glitz of Las Vegas behind and drive toward Santa Monica where you will enjoy a two-night stay. To continue following Route 66 you have to drive via Barstow for a visit to Casa Del Decierto (Desert House). This restored Harvey House houses the Route 66 Museum. After a brief stop, continue to Santa Monica. Both a seaside town and bustling city, Santa Monica has activities for both young and old, from beach games and bike paths to art galleries and nightclubs, from shopping and fitness to theater and concerts. Santa Monica’s cultural offerings run the gamut, with over 75 museums and art galleries within the walkable 8.3 square mile city limits. Not to mention the array of public art and sculpture exhibited in the streets. Visit Santa Monica Pier, once known as the "finish line" of legendary Route 66. It features an aquarium, an amusement park and the famous Hippodrome building, a mix of California, Byzantine and Moorish architecture that has been featured in many films.

Accommodations: Carmel by the Sea or similar (2 nights)

Day 15 | Santa Monica, CA

Distance: 0.00 miles / 0.0 km

Today, Spend some time at the beach; with 3.5 miles of Southern California beaches and over 300 days of sunshine, the Santa Monica Beach is a welcome retreat for vacationers and locals alike with a range of activities for everyone. Swimming, surffing, volleyball, skating and biking are among the favorite beach-side pasttimes of this area. In the evening, countless dining experiences are available; Santa Monica is the reputed birthplace of “California” and “fusion” cuisines which are marked by an artistic blending of culinary styles and the freshest of organic ingredients. Or, you can choose to explore the neighboring City of Angels. Visit the glitz and glamour of Hollywood. Shop the famous Rodeo Drive, where luxury retail commands the street. Have lunch in Venice Beach, home to famous Muscle Beach, where the sand and surf are secondary to the lively scene of people that inhabit the sidewalk.

Day 16 | Santa Monica – Los Angeles International Airport, CA

Distance: 12.00 miles / 19.3 km

Depart at leisure for the Los Angeles International Airport. Drop-off rental car.